Pretty Girl
by MinaZareen
Summary: Wincest/Weecest. Pretty much PWP. Not age specific but I'm thinking Sam is in his early teens. Contains crossdressing, panties and dirty talk.


Sam fingers were trembling as he trailed them over the light purple fabric of the short skirt. He turned to the side, looking more closely at himself in the bathroom mirror.

He had been skeptical when Dean had suggested this, and he was still feeling slightly uncomfortable but Dean had been right; he looked good with the thin material of the shirt clinging to his skin, the skirt sitting low on his hips and his bangs falling into his face.

He took a deep breath and gave his reflection an encouraging smile, but his hand was still shaky when he opened the door and peeked outside.

Dean was sitting on the edge of the dingy motel bed, his hair disheveled and his lips still flushed from their previous make-out session and Sam's heart jumped at the sight.

"C'mere, Sammy, wanna see you."

Sam cast his eyes to the floor and slowly stepped out into the bedroom. He had never felt this self-conscious before. He could hear Dean get up from the bed and move closer to him. He lifted his chin and Sam bit his lip when he was forced to look up at his big brother.

Dean let his hands glide through the soft strands of Sam's hair and smiled. "Look so beautiful Sammy, knew you'd look hot in these." His hands travelled down to Sam's thighs and played with the seam of the skirt.

"You alright?" he asked, his face falling at the nervousness in Sam's eyes.

Sam couldn't help but chuckle at the worried look on Dean's face. "Yeah, I'm fine, just a bit nervous… Wasn't sure you'd like it."

Dean leaned down and brushed his lips over Sam's in a soft kiss. He took Sam's hand and brought it up to the bulge in his pants so Sam could feel his erection through the denim. "Don't worry; I love it," he smirked, "you're such a cute, little girl." He grabbed Sam's waist with both hands, lifting him up in one swift motion and carrying him over to the bed. He pushed his little brother down onto the mattress and Sam scooted up so his head was resting on the pillows. Dean climbed onto the bed next to him and pulled him into a slow, passionate kiss before he drew back and motioned for Sam to turn onto his stomach.

Sam quickly complied, turning over and burying his face in the pillows.

Dean straddled Sam's thighs and leaned down to kiss the back of his neck. "Gonna take great care of you, sweetheart, gonna make you feel so good."

Sam could feel his brother's breath on his skin and the slight stubble on Dean's jaw and squirmed against the mattress. Dean moved further down his body and slid a hand under the skirt, but froze when his fingers trailed over soft, satiny material.

"You wearing those panties I bought you?" Dean's voice was low and breathy and it sent shivers down Sam's spine. "Such a good little slut for your brother, so obedient. Bet you'd do anything to feel my dick inside of you, nice and deep. Want me to fuck you, Sammy?"

Sam groaned and nodded. His cock was rock hard in his panties and he ground his hips down to get some friction.

Dean pushed his skirt up, exposing Sammy's cute little ass and squeezing the cheeks before he pulled the pink satin aside and spread them. He leaned down so his face was level with his brother's ass, breathing against the tight, pink hole. Sam whimpered and bucked his hips when Dean flicked his tongue over the sensitive skin.

"Taste so good Sammy," Dean hummed, "gonna get you all nice and wet for me." He sucked on the rim of Sam's entrance and then dipped his tongue inside, feeling the muscles flutter and then relax around the intrusion.

Dean pushed his tongue a little deeper and hummed at the taste. Sam was a quivering mess by the time Dean's tongue slid in and out of him in a steady rhythm and he gripped the sheets tighter and craned his neck so he could look back at his brother over his shoulder.

"D-Dean I- ah fuck, more, Dean please, I need more-"

Dean drew back and Sam shuddered at the familiar sound of a lube packet being ripped open, hissing when the cold liquid dripped onto his skin.

Dean poured the contents of the packet over Sammy's hole, using his index finger to push some of it inside and brushing the tip of his finger over Sam's prostate, making him gasp and clench around him. He inserted another finger and spread them, stretching his little brother's tight entrance.

"Get on your knees, baby girl."

Sam's arms gave out when he tried to get up but Dean gripped his waist and pulled him back onto his knees, his ass up in the air and his face still buried between the pillows. He could feel a third finger being pushed into him, stretching him wide and he gasped every time the fingers hit his sweet spot, rocking his hips back onto them.

"Should see yourself, Sammy," Dean panted, his free hand on Sam's back, pushing him down onto the bed, "fucking yourself on my fingers like the desperate slut you are. Won't even have to take off those panties when I sink my cock into that tight ass."

Sam couldn't help but moan into the sheets. He turned his head to the side, his cheeks flushed and his mouth slightly agape, breathing heavily as he tried to get enough air into his lungs. "Please, I need- _oh god_, I'm ready Dean, just- just fuck me already, _ah_, gonna be so good I promise-"

Dean groaned and all at once his fingers were gone and Sam damn near sobbed at the sudden loss. He could feel some of the lube running down his thighs and his cock twitched as he thought about the view his brother was having of him.

He heard the sound of a zipper and the rustling of the denim as Dean pushed his jeans down to his knees together with his boxers. His cock was painfully hard by the time he wrapped his hand around the thick shaft and started to slowly stroke himself, moaning at the sensation of his lube-slick fingers around his length.

Sam whimpered when the head of Dean's cock nudged at his entrance, not quite pushing inside.

"Got such an eager hole, baby, so nice and wet and ready, just waiting for me to fill you up and fuck you into the mattress." He placed one hand on Sam's shoulder and grabbed his hip with the other as he sank his cock into him in one smooth motion. Sam arched his back and whined. He felt so full, his whole body trembling with the sensation of his big brother's heavy cock filling him up. Dean paused for a moment and ran a soothing hand through Sammy's hair, allowing his little brother to get used to the sensation of his hot length stretching him.

"Dean," Sam whimpered, his voice muffled by the pillows as he clenched around his brother's cock, "_oh god_, you're big, _ah_, y-you can go harder, please, feels so good."

Sam cried out when Dean's hand clasped his neck and he gave a sharp thrust, pushing Sammy further into the mattress. "You like that, slut? Like having my dick inside of you? Gonna fuck you so hard, you're gonna feel me for days."

It had taken a while for Dean to be comfortable talking to Sammy like this without feeling like he was taking advantage of him, but Sam had assured him that he wanted this, that he knew Dean loved him and that they could always stop as soon as one of them was starting to feel uneasy. Dean still insisted on a safeword whenever they were roleplaying and Sam was fine with it even though he knew he'd never have to say anything. Dean had never done anything Sam didn't enjoy and Sam knew he could trust his big brother completely.

He grabbed the bed sheets tighter and pushed his hips back against Dean's, encouraging him to move.

Dean picked up the pace and Sam whimpered every time Dean hit his prostate. He could feel the heat rush through his body, his cock leaking precome in his panties.

"Fuck, you're tight" Dean moaned. He let go of Sam's hip and slid his hand lower, letting his thumb brush over the place where Sammy's skin stretched around his dick, watching himself push into his baby brother. The sight nearly pushed him over the edge.

"D-Dean, _please-_" Sam panted as another thrust pushed him forward and made his vision blur.

Dean's hand found Sam's cock and he started to rub him through the panties, each stroke in time with his thrusts. Sam moaned and cried Dean's name when he came, the fabric of the panties wet and sticky with his come. He clenched around Dean's dick and Dean groaned, grabbing Sammy's hips with both hands as he slammed into him harder. "_Oh fuck_, Sammy, I'm so close, gonna come inside you, gonna get you all wet inside like a good little slut. You want that, Sammy?"

Sam squirmed, his hole clenching even tighter, sweet, little noises falling from his lips as Dean fucked him.

Dean didn't last much longer. His hips stuttered and he pulled Sam back onto his cock, burying himself completely in the tight heat, his cock throbbing as he came inside his little brother.

Dean panted against Sam's neck, trying to catch his breath before he gently pulled out.

Sam hissed when the head of Dean's cock slipped out of him. His ass felt used and sore and he could feel Dean's come trickle down his inner thighs. Dean flopped down next to him on the bed and pulled him close so Sam could rest his head on Dean's shoulder. He ran his fingers through Sam's sweaty strands and pressed a light kiss to his forehead. "You ok?"

"Yeah, great, just a little tired" Sam smiled, "that was perfect, Dean, I love you." He nuzzled under Dean's chin and kissed his neck.

Dean grinned and snuggled closer to his baby brother. "Love you too, Sammy."


End file.
